Many-membered Carbon Rings. XVIII. Synthesis and Acyloin Cyclization of δ,δ-Diphenylazelaic Ester<sup>1</sup>

Blomquist, A. T.; Buck, C. J.

doi:10.1021/ja01512a041

Cited by 11 publications

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“…In order to investigate the formation of adducts 5-7,11, and 12 in the reaction of -acetoxyNPYR with DNA, we developed conditions (HPLC system 4) to separate them. This system also separated 14 from the other compounds, as illustrated in Figure 5A. HPLC analysis of the products formed by neutral thermal hydrolysis of DNA that had been incubated with -acetoxyNPYR and esterase for 12 Time (h) Figure 6.…”

Section: Resultsmentioning

confidence: 95%

“…HPLC separation using system 4 of (A) standards and (B) products released upon neutral thermal hydrolysis of DNA that had been allowed to react with -acetoxyNPYR in the presence of esterase. Upon NaBH4 treatment of the thermal hydrolysate, adduct 6 disappeared, adduct 14 formed, and the other adducts remained unchanged.…”

Section: Resultsmentioning

confidence: 99%

“…Preparation of 7-(3-Carboxypropyl)guanine (7) and 7-(4-Hydroxybutyl)guanine (14). A mixture of TAG (409 mg, propyl) guanine (15 mg, 0.06 mmol, 60% yield) precipitated as a white solid, mp >280 °C [lit.…”

Section: Methodsmentioning

confidence: 99%

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Formation of acyclic and cyclic guanine adducts in DNA reacted with .alpha.-acetoxy-N-nitrosopyrrolidine

Wang

Chung

Hecht

1989

Chem. Res. Toxicol.

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This paper describes the reaction of alpha-acetoxy-N-nitrosopyrrolidine with DNA to produce six adducts: two new acyclic adducts, 7-(4-oxobutyl)guanine (6) and 7-(3-carboxypropyl)guanine (7), and four cyclic adducts--the exocyclic 7,8-guanine adducts 5, 11, and 12 and an exocyclic 1,N2-guanine adduct 13--which we have previously characterized. The initial purpose of this study was to carry out an independent synthesis to verify the structure of adduct 5, which is formed in liver DNA of rats treated with N-nitrosopyrrolidine. This was accomplished by the reaction of 2',3',5'-triacetylguanosine with 4-iodobutyraldehyde. This reaction also produced 7-(4-oxobutyl)guanine (6), which underwent air oxidation to 7. The new adducts were characterized by their proton NMR, UV, and mass spectral properties, by chemical transformations, and by independent syntheses. The six adduct standards were used to develop HPLC systems for their analysis as products of the reaction of alpha-acetoxy-N-nitrosopyrrolidine with DNA. Studies on their rates of formation and stability in DNA were carried out. The major products were 7-(4-oxobutyl)guanine (6) and the exocyclic 7,8-guanine adduct 5, which apparently were both formed mainly by reaction with DNA of 4-oxobutanediazohydroxide (4). Their concentrations were maximal after 6 h and subsequently decreased due to depurination. Little evidence was obtained for cyclization of 6 to 5, at the base level or in DNA. The concentrations of adducts 11-13, which were formed by reaction with DNA of crotonaldehyde (10), increased gradually over the 36-h time period studied.(ABSTRACT TRUNCATED AT 250 WORDS)

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Section: Resultsmentioning

confidence: 95%

Section: Resultsmentioning

confidence: 99%

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Formation of acyclic and cyclic guanine adducts in DNA reacted with .alpha.-acetoxy-N-nitrosopyrrolidine

Wang

Chung

Hecht

1989

Chem. Res. Toxicol.

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“…One attempted preparation of the corresponding 6-methylene compound yielded a mixture of products, the major one of which seemed to be bicyclo proof was obtained (90). Other more highly substituted medium ring acyloins have been prepared and most have involved cyclononane (11,14,22).…”

Section: C6h5ch=chc02c2h6mentioning

confidence: 99%

The Acyloin Condensation as a Cyclization Method

Finley¹

1964

Chem. Rev.

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The Acyloin Condensation

2011

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The acyloin condensation usually involves the reductive dimerization of a carboxylic ester, although acid chlorides and the anhydrides have been used. The reducing agent is in an alkali metal and the product is an ene‐diolate. Two gram‐atoms of metal are required for each mole of ester with the concomitant formation of a mole of akoxide and one‐half mole of the ene‐diolate. Oxidation of acyloins to diketoes can be accomplished by a variety of reagents. Acyloins can be reduced to ketones by various modifications of the Clemmenson technique. Under mild conditions the ketone will dominate. This chapter presents a complete picture of both the linear and cyclic acyloin condensation with particular emphasis on developments since 1960. The discussion is closely limited to the acyloin condensation and its modifications.

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Many-membered Carbon Rings. XVIII. Synthesis and Acyloin Cyclization of δ,δ-Diphenylazelaic Ester¹

Cited by 11 publications

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Formation of acyclic and cyclic guanine adducts in DNA reacted with .alpha.-acetoxy-N-nitrosopyrrolidine

Formation of acyclic and cyclic guanine adducts in DNA reacted with .alpha.-acetoxy-N-nitrosopyrrolidine

The Acyloin Condensation as a Cyclization Method

The Acyloin Condensation

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Many-membered Carbon Rings. XVIII. Synthesis and Acyloin Cyclization of δ,δ-Diphenylazelaic Ester1

Cited by 11 publications

References 0 publications

Formation of acyclic and cyclic guanine adducts in DNA reacted with .alpha.-acetoxy-N-nitrosopyrrolidine

Formation of acyclic and cyclic guanine adducts in DNA reacted with .alpha.-acetoxy-N-nitrosopyrrolidine

The Acyloin Condensation as a Cyclization Method

The Acyloin Condensation

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Many-membered Carbon Rings. XVIII. Synthesis and Acyloin Cyclization of δ,δ-Diphenylazelaic Ester¹